Chat services such as Yahoo! Messenger, MSN Messenger, and the like are popular means by which users communicate via the Internet. However, for mobile devices such as mobile telephones and Personal Digital Assistants (PDAs), access to the Internet may be limited due to cost or non-existent. Thus, since many mobile devices have local wireless interfaces, such as a Bluetooth interface, it is desirable to establish local chat sessions between mobile devices using their local wireless interfaces. However, unlike traditional Internet-based chat services, a chat service operating via the local wireless interface of a mobile device may have access to only a limited number of other mobile devices due to the limited coverage area of the local wireless interface. Further, the user may have no knowledge of the users of the other mobile devices and may be unable to make an intelligent determination as to whether he or she should initiate a local chat session with a user of one of the other mobile devices. As such, there remains a need for a system and method of establishing a local chat session wherein an intelligent decision is made as to whether to initiate the local chat session either automatically by the device or through interaction with the user.